Corrosion-resistant epoxidized vegetable oil can interior coating

ABSTRACT

A coating composition comprising epoxidized vegetable oil, an amine terminated polyamide and a silicone resin is disclosed. Substrates coated at least in part with such coatings are also disclosed.

FIELD OF THE INVENTION

The present invention is directed to coating compositions comprisingepoxidized vegetable oil, an amine terminated polyamide and a silicone.Substrates, including packages, coated at least in part with such acoating are also within the scope of the present invention.

BACKGROUND OF THE INVENTION

The application of various polymeric coatings to metallic substrates,including metal cans such as food, beverage and cosmetic containers, toretard or inhibit corrosion is well established. Coatings are applied tothe interior of such containers to prevent the contents from contactingthe metal of the container. Contact between the metal and the food,beverage or cosmetic can lead to corrosion of the metal container, whichcan then contaminate the product. This is particularly true when thecontents of the container are acidic in nature, such as tomato-basedproducts and soft drinks.

Certain coatings, particularly in the packaging industry, must undergoextreme stresses in the course of preparation and use of the packagingcontainers. In addition to flexibility, packaging coatings may also needresistance to chemicals, solvents, and pasteurization processes used inthe packaging of beer and other beverages, and may also need towithstand retort conditions commonly employed in food packaging. Inaddition to corrosion protection, coatings for food and beveragecontainers should be non-toxic, and should not adversely affect thetaste of the food or beverage in the can. Resistance to “popping”,“blushing” and/or “blistering” may also be desired.

Bisphenol A (“BPA”) contributes to many of the properties desired inpackaging coating products. The use of BPA and related products such asbisphenol A diglycidyl ether (“BADGE”), however, has recently come underscrutiny in the packaging industry. Substantially BPA-free coatingshaving properties comparable to coatings comprising BPA are thereforedesired. A reduced use of formaldehyde in coatings is also desired.

SUMMARY OF THE INVENTION

The present invention is directed to a coating comprising: a. epoxidizedvegetable oil; b. an amine terminated polyamide; and c. a siliconeresin; wherein the composition comprises 5 wt % or greater vegetable soybean oil based on the total solid weight of the composition.

DETAILED DESCRIPTION OF THE INVENTION

The present invention is directed to a coating composition comprising anepoxidized vegetable oil, an amine terminated polyamide, and a siliconeresin.

Any suitable epoxidized vegetable oil (“EVO”) can be used, and caneither be obtained commercially or prepared by epoxidizing a vegetableoil. Vegetable oils include but are not limited to corn, cottonseed,linseed, rapeseed, tall, palm, peanut, sesame, sunflower, and soy.Epoxidized soy bean oil (“ESBO”) is particularly suitable and iscommercially available from a number of sources, such as Hallstar, asPLASTHALL ESO, and Arkema, in its VIKOFLEX line, such as VIKOFLEX 7170.ESBO and other epoxidized vegetable oils are known as plasticizers inmaterials using vinyl chlorides. It was surprisingly discovered that acoating composition comprising EVO with an amine terminated polyamideimparts greater corrosion resistance to a metal substrate when suchcomposition is cured as compared to a cured composition having only EVOor only an amine terminated polyamide. The amount of EVO in the presentcompositions can vary, such as 5 wt % or greater, 7.5 wt % or greater,10 wt % or greater or 12 wt % or greater, and such as 20 wt % or loweror 15 wt % or lower, with wt % based on the total solids weight of thecomposition. A wt % of 10-12 may be particularly suitable.

Any amine terminated polyamide can be used according to the presentinvention. The polyamide, for example, can be based on a dimer acid.Suitable amine values for the polyamide can vary based on the needs ofthe user and can range, for example from 220 to 250, such as 232 to 242,as determined by titration with HBr in HBr/Acetic acid using methylviolet indicator. The viscosity of the polyamide can also vary, and canrange, for example, from 400 to 800 poise, such as 550 to 700 poise,when measured with a #3 spindle at 20 RPM by Brookfield viscometer at40° C. Polyamides are widely commercially available, such as from Hexionin their EPIKURE line. The amount of amine terminated polyamide in thepresent compositions can vary, such as 2 wt % or greater, 3.5 wt % orgreater, or 5 wt % or greater, and such as 15 wt % or lower, 12.5 wt %or lower, or 10 wt % or lower, with wt % based on the total solidsweight of the composition. A wt % of 3 to 12 may be particularlysuitable.

The silicone resin used according to the present invention may also varybased on the needs of the user. Combinations of silicone resins may alsobe used. Particularly suitable are silsesquioxane resins, includingsilanol functional silsesquioxanes. Suitable silicone resins, includingsilanol functional silsesquioxanes, are commercially available from DowChemical in their RSN line. RSN 217, for example, is a fully phenylatedsilanol functional silsesquioxane and with a degree of substitution of1.0. RSN 233, for example, is a silanol functional silsesquioxane with aphenyl to methyl ratio of 1.3:1 and a degree of substitution of 1.15.RSN 255, for example, is also a silanol functional silsesquioxane with aphenyl to methyl ratio of 0.84:1 and a degree of substitution of 1.05.All of these values are as reported by the manufacturer, Dow. The amountof silicone resin in the present compositions can vary, such as 10 wt %or greater, 15 wt % or greater, 20 wt % or greater or 25 wt % orgreater, and such as 60 wt % or lower or 50 wt % or lower or 40 wt % orlower, with wt % based on the total solids weight of the composition. Awt % or 15 to 50 may be particularly suitable.

The coating compositions of the present invention may further comprise afilm-forming component. A film forming component may include, forexample, a film forming resin and a crosslinker therefor. Any filmforming resin can be used according to the present invention. Thefilm-forming resin can comprise, for example, an acrylic polymer, apolyester polymer, a polyurethane polymer, a polyamide polymer, apolyether polymer, a polysiloxane polymer, copolymers thereof, andmixtures thereof. Generally, these polymers can be any polymers of thesetypes made by any method known to those skilled in the art. Suchpolymers may be solvent-borne or water-dispersible, emulsifiable, or oflimited water solubility. The film forming resin will typically havefunctional groups including, for example, carboxylic acid groups, aminegroups, epoxide groups, hydroxyl groups, thiol groups, carbamate groups,amide groups, urea groups, isocyanate groups (including blockedisocyanate groups) mercaptan groups, and combinations thereof.Appropriate mixtures of film-forming resins may also be used in thepreparation of the present compositions. The film forming component mayalso comprise a crosslinker, having functional groups reactive with thefunctional groups on the resin. One skilled in the art can select anappropriate crosslinker based on this functionality from crosslinkerssuch as melamine such as melamine formaldehyde resin, phenolic such asphenolic formaldehyde resin and/or cresol formaldehyde phenolic resin,carbodiimide, hydroxyalkylamide, hydroxyalkyurea, isocyanate, blockedisocyanate, benzoguanamine, TGIC, epoxies, oxazolines, and the like. Thefilm forming resin may also be self crosslinking; that is, the resinwill react with itself to cure. Examples of such resins includepolysiloxane resins that contain silanol (Si—OH), alkoxy groups(Si—O—R), or acetoxy groups (Si—O—COCH3), which can condense or becomereactive due to the presence of moisture and heat to self-condense.) Thefilm forming resin can be used in an amount of 20 wt % or greater, suchas 30 wt % or greater or 40 wt % or greater, and such as 60 wt % orlower, 50 wt % or lower or 40 wt % or lower, with wt % based on thetotal solid weight of the composition. A wt % of 20 to 50 may beparticularly suitable.

A particularly suitable film forming resin is an acrylic resin. Theacrylic resin, for example, may be formed by using any number of acrylicmonomers, including styrene, alkyl (meth) acrylates such as ethyl(meth)acrylate, methyl (meth)acrylate, and butyl (meth)acrylate,functional acrylates such as hydroxyethyl (meth)acrylate, cyclic andpolycyclic (meth)acrylics such as benzyl (meth)acrylate, cyclohexyl(meth)acrylate and isobornyl (meth)acrylate, and acrylamides such asN-butoxy methyl acrylamide (N-BMA). For example, an acid functional(meth)acrylic acid and an alkyl (meth)acrylate may each be used.Mixtures of (meth)acrylic resins can also be used. It will be understoodthat (meth)acrylic and like terms refers to both methacrylic andacrylic. According to the present invention, the acrylic resin and/orthe coating compositions themselves may exclude hydroxyl functionalacrylic monomers, styrene and/or vinyl chloride monomers. The acrylicresin and/or the coating compositions themselves may exclude ethylacrylate and/or acrylamides, such as N-BMA. In addition, when using anacrylic resin in the present compositions, the (meth)acrylic resin willnot generally contain unreacted unsaturation. That is, reaction of the(meth)acrylic monomers in the formation of the (meth)acylic resin willconsume the unsaturation. Thus, the (meth)acrylic resins used accordingto the present invention are not radiation curable, and any residualunsaturation that might remain in the (meth)acrylic resin upon reactionof the monomers is not enough to render the (meth)acrylic radiationcurable.

As noted above, the present compositions may comprise a crosslinker,including one or more crosslinkers. Benzoguanamine is a particularlysuitable crosslinker and, if used, can be present in the composition inan amount of 5 wt % or greater, such as 7.5 wt % or greater or 10 wt %or greater, and such as 35 wt % or less, 30 wt % or less, or 25 wt % orless, with wt % based on the total solids weight of the composition. Awt % of 10 to 30 is particularly suitable.

A phenolic resin or crosslinker, such as a phenol formaldehyde resin,can also be included in the present compositions, either alone or inconjunction with another crosslinker. For certain applications, however,it may be desired to minimize, if not eliminate, the amount of phenolicused in coating compositions in the packaging industry. It will beappreciated that phenolics are often made with formaldehyde andtherefore bring formaldehyde into the composition. It was surprisinglydiscovered that the amount of phenolic can be minimized, and eveneliminated, in compositions also comprising EVO, particularly ESBO,amine terminated polyamide, and silicone resin, such as described above.For example, a typical commercial coating composition may contain 50 wt% phenolic. Coating compositions of the present invention may contain 30wt % or less of phenolic resin, such as 25 wt % or less, 20 wt % orless, 15 wt % or less, 10 wt % or less, 5 wt % or less, 2 wt % or less,or 1 wt % or less. The compositions may also be completely free ofphenolic, which will be understood as referring to being completely freeof any added phenolic, with any trace amounts of phenolic brought inthrough other coating components.

As noted above, the present compositions comprise EVO. The EVO can bepre-reacted with another coating component or can react with anothercoating component upon cure of the coating composition. For example, itmay be desired that the EVO is not pre-reacted with any of the othercoating components in the composition and undergoes reaction with theamine terminated polyamide only upon heat cure. Upon curing with heatthe oxirane functionality of the EVO reacts with the primary amine ofthe amine terminated polyamide to form a hydroxyl and a secondary amine.The reaction during cure is particularly suitable for applicationsregulated by the FDA. Alternatively, and particularly when FDAconsiderations are not relevant, the EVO can be pre-reacted with theamine terminated polyamide, or any other coating component, prior tocure. The EVO does not undergo transesterification with any othercomponent, and is not a plasticizer or hydrogen chloride scavenger.

The coating composition may comprise one or more solvents includingwater or organic solvents. Suitable organic solvents include glycols,glycol ether alcohols, alcohols, ketones, and aromatics, such as xyleneand toluene, acetates, mineral spirits, naphthas and/or mixturesthereof. “Acetates” include the glycol ether acetates. The solvent canbe a non-aqueous solvent. “Non-aqueous solvent” and like terms meansthat less than 50% of the solvent is water. For example, less than 10%,or even less than 5% or 2%, of the solvent can be water. It will beunderstood that mixtures of solvents, including or excluding water in anamount of less than 50%, can constitute a “non-aqueous solvent”. Thecomposition may be aqueous or water-based. This means that 50% or moreof the solvent is water. These embodiments have less than 50%, such asless than 20%, less than 10%, less than 5% or less than 2% solvent. Thecoating compositions of the present invention are more suitably waterbased.

If desired, the compositions can comprise other optional materials wellknown in the art of formulating, such as colorants, plasticizers,abrasion resistant particles, anti-oxidants, hindered amine lightstabilizers, UV light absorbers and stabilizers, surfactants, flowcontrol agents, thixotropic agents, fillers, organic cosolvents,reactive diluents, catalysts, grind vehicles, slip agents, moisturescavenger and other customary auxiliaries.

As used herein, the term “colorant” means any substance that impartscolor and/or other opacity and/or other visual effect to thecomposition. The colorant can be added to the coating in any suitableform, such as discrete particles, dispersions, solutions and/or flakes.A single colorant or a mixture of two or more colorants can be used inthe coatings of the present invention. Particularly suitable forpackaging coatings are those approved for food contact, such as titaniumdioxide; iron oxides, such as black iron oxide; carbon black;ultramarine blue; phthalocyanines, such as phthalocyanine blue andphthalocyanine green; graphite fibrils; ferried yellow; quindo red; andcombinations thereof, and those listed in Article 178.3297 of the Codeof Federal Regulations, which is incorporated by reference herein.

Example colorants include matting pigments, dyes and tints, such asthose used in the paint industry and/or listed in the Dry ColorManufacturers Association (DCMA), as well as special effectcompositions. A colorant may include, for example, a finely dividedsolid powder that is insoluble but wettable under the conditions of use.A colorant can be organic or inorganic and can be agglomerated ornon-agglomerated. Colorants can be incorporated into the coatings bygrinding or simple mixing. Colorants can be incorporated by grindinginto the coating by use of a grind vehicle, such as an acrylic grindvehicle, the use of which will be familiar to one skilled in the art.

Example pigments and/or pigment compositions include, but are notlimited to, carbazole dioxazine crude pigment, azo, monoazo, disazo,naphthol AS, salt type (lakes), benzimidazolone, condensation, metalcomplex, isoindolinone, isoindoline and polycyclic phthalocyanine,quinacridone, perylene, perinone, diketopyrrolo pyrrole, thioindigo,anthraquinone, indanthrone, anthrapyrimidine, flavanthrone, pyranthrone,anthanthrone, dioxazine, triarylcarbonium, quinophthalone pigments,diketo pyrrolo pyrrole red (“DPPBO red”), titanium dioxide, carbonblack, carbon fiber, graphite, other conductive pigments and/or fillersand mixtures thereof. The terms “pigment” and “colored filler” can beused interchangeably.

Example dyes include, but are not limited to, those that are solventand/or aqueous based such as acid dyes, azoic dyes, basic dyes, directdyes, disperse dyes, reactive dyes, solvent dyes, sulfur dyes, mordantdyes, for example, bismuth vanadate, anthraquinone, perylene aluminum,quinacridone, thiazole, thiazine, azo, indigoid, nitro, nitroso,oxazine, phthalocyanine, quinoline, stilbene, and triphenyl methane.

Example tints include, but are not limited to, pigments dispersed inwater-based or water-miscible carriers such as AQUA-CHEM 896commercially available from Degussa, Inc., CHARISMA COLORANTS andMAXITONER INDUSTRIAL COLORANTS commercially available from AccurateDispersions division of Eastman Chemicals, Inc.

As noted above, the colorant can be in the form of a dispersionincluding, but not limited to, a nanoparticle dispersion. Nanoparticledispersions can include one or more highly dispersed nanoparticlecolorants and/or colorant particles that produce a desired visible colorand/or opacity and/or visual effect. Nanoparticle dispersions caninclude colorants such as pigments or dyes having a particle size ofless than 150 nm, such as less than 70 nm, or less than 30 nm.Nanoparticles can be produced by milling stock organic or inorganicpigments with grinding media having a particle size of less than 0.5 mmExample nanoparticle dispersions and methods for making them areidentified in U.S. Pat. No. 6,875,800 B2, which is incorporated hereinby reference. Nanoparticle dispersions can also be produced bycrystallization, precipitation, gas phase condensation, and chemicalattrition (i.e., partial dissolution). In order to minimizere-agglomeration of nanoparticles within the coating, a dispersion ofresin-coated nanoparticles can be used. As used herein, a “dispersion ofresin-coated nanoparticles” refers to a continuous phase in which isdispersed discreet “composite microparticles” that comprise ananoparticle and a resin coating on the nanoparticle. Exampledispersions of resin-coated nanoparticles and methods for making themare described, for example, in U.S. Pat. No. 7,605,194 at column 3, line56 to column 16, line 25, the cited portion of which being incorporatedherein by reference.

Example special effect compositions that may be used include pigmentsand/or compositions that produce one or more appearance effects such asreflectance, pearlescence, metallic sheen, phosphorescence,fluorescence, photochromism, photosensitivity, thermochromism,goniochromism and/or color-change. Additional special effectcompositions can provide other perceptible properties, such as opacityor texture. For example, special effect compositions can produce a colorshift, such that the color of the coating changes when the coating isviewed at different angles. Example color effect compositions areidentified in U.S. Pat. No. 6,894,086, incorporated herein by reference.Additional color effect compositions can include transparent coated micaand/or synthetic mica, coated silica, coated alumina, a transparentliquid crystal pigment, a liquid crystal coating, and/or any compositionwherein interference results from a refractive index differential withinthe material and not because of the refractive index differentialbetween the surface of the material and the air.

A photosensitive composition and/or photochromic composition, whichreversibly alters its color when exposed to one or more light sources,can be used in the coating of the present invention. Photochromic and/orphotosensitive compositions can be activated by exposure to radiation ofa specified wavelength. When the composition becomes excited, themolecular structure is changed and the altered structure exhibits a newcolor that is different from the original color of the composition. Whenthe exposure to radiation is removed, the photochromic and/orphotosensitive composition can return to a state of rest, in which theoriginal color of the composition returns. For example, the photochromicand/or photosensitive composition can be colorless in a non-excitedstate and exhibit a color in an excited state. Full color-change canappear within milliseconds to several minutes, such as from 20 secondsto 60 seconds. Example photochromic and/or photosensitive compositionsinclude photochromic dyes.

The photosensitive composition and/or photochromic composition can beassociated with and/or at least partially bound to, such as by covalentbonding, a polymer and/or polymeric materials of a polymerizablecomponent. In contrast to some coatings in which the photosensitivecomposition may migrate out of the coating and crystallize into thesubstrate, the photosensitive composition and/or photochromiccomposition associated with and/or at least partially bound to a polymerand/or polymerizable component in accordance with the present inventionhave minimal migration out of the coating. Example photosensitivecompositions and/or photochromic compositions and methods for makingthem are identified in U.S. Pat. No. 8,153,344, and incorporated hereinby reference.

In general, the colorant can be present in any amount sufficient toimpart the desired visual and/or color effect. The colorant may comprisefrom 1 to 65 wt % of the present compositions, such as from 3 to 40 wt %or 5 to 35 wt %, with weight percent based on the total weight of thecomposition.

An “abrasion resistant particle” is one that, when used in a coating,will impart some level of abrasion resistance to the coating as comparedwith the same coating lacking the particles. Suitable abrasion resistantparticles include organic and/or inorganic particles. Examples ofsuitable organic particles include but are not limited to diamondparticles, such as diamond dust particles, and particles formed fromcarbide materials; examples of carbide particles include but are notlimited to titanium carbide, silicon carbide and boron carbide. Examplesof suitable inorganic particles include but are not limited to silica;alumina; alumina silicate; silica alumina; alkali aluminosilicate;borosilicate glass; nitrides including boron nitride and siliconnitride; oxides including titanium dioxide and zinc oxide; quartz;nepheline syenite; zircon such as in the form of zirconium oxide;buddeluyite; and eudialyte. Particles of any size can be used, as canmixtures of different particles and/or different sized particles. Forexample, the particles can be microparticles, having an average particlesize of 0.1 to 50, 0.1 to 20, 1 to 12, 1 to 10, or 3 to 6 microns, orany combination within any of these ranges. The particles can benanoparticles, having an average particle size of less than 0.1 micron,such as 0.8 to 500, 10 to 100, or 100 to 500 nanometers, or anycombination within these ranges.

Any slip agent can be used according to the present invention such asthose commercial available from BYK Chemie or Dow Corning. A wax canalso be used such as polyolefin wax, silicone or paraffin.

The coating compositions of the present invention, may be substantiallyfree, may be essentially free and/or may be completely free of bisphenolA and epoxy compounds derived from bisphenol A (“BPA”), such asbisphenol A diglycidyl ether (“BADGE”). Such compounds are sometimesreferred to as “BPA non intent” because BPA, including derivatives orresidues thereof, are not intentionally added but may be present intrace amounts because of impurities or unavoidable contamination fromthe environment. The coating compositions can also be substantially freeand may be essentially free and/or may be completely free of bisphenol Fand epoxy compounds derived from bisphenol F, such as bisphenol Fdiglycidyl ether (“BFDGE”). The term “substantially free” as used inthis context means the components and/or the coating compositionsthemselves contain less than 1000 parts per million (ppm), “essentiallyfree” means less than 100 ppm and “completely free” means less than 20parts per billion (ppb) of any of the above mentioned compounds,derivatives or residues thereof.

The present compositions can be applied to any substrates known in theart, for example, automotive substrates, marine substrates, industrialsubstrates, packaging substrates, wood flooring and furniture, apparel,electronics including housings and circuit boards and including consumerelectronics such as housings for computers, notebooks, smartphones,tablets, televisions, gaming equipment, computer equipment, computeraccessories, MP3 players, glass and transparencies, sports equipmentincluding golf balls, and the like. Accordingly, the present inventionis further directed to a substrate coated at least in part with any ofthe coating compositions described above. These substrates can be, forexample, metallic or non-metallic. Metallic substrates include tin,steel, tin-plated steel, chromium passivated steel, galvanized steel,aluminum, aluminum foil. Metal sheet as used herein refers to flat metalsheet and coiled metal sheet, which is coiled, uncoiled for coating andthen re-coiled for shipment to a manufacturer. Non-metallic substratesinclude polymeric, plastic, polyester, polyolefin, polyamide,cellulosic, polystyrene, polyacrylic, poly(ethylene naphthalate),polypropylene, polyethylene, nylon, EVOH, polylactic acid, other “green”polymeric substrates, poly(ethyleneterephthalate) (“PET”),polycarbonate, polycarbonate acrylobutadiene styrene (“PC/ABS”),polyamide, wood, veneer, wood composite, particle board, medium densityfiberboard, cement, stone, glass, paper, cardboard, textiles, leatherboth synthetic and natural, and the like. The substrate can be one thathas been already treated in some manner, such as to impart visual and/orcolor effect. Suitable substrates can include those in which powdercoatings are typically applied.

The compositions of the present invention can be applied by any meansstandard in the art, such as electrocoating, spraying, electrostaticspraying, dipping, rolling, brushing, and the like.

The compositions can be applied to a dry film thickness of 0.04 mils to4 mils, such as 0.3 to 2 or 0.7 to 1.3 mils. The compositions can alsobe applied to a dry film thickness of 0.1 mils or greater, 0.5 mils orgreater 1.0 mils or greater, 2.0 mils or greater, 5.0 mils or greater,or even thicker. In some applications, a dry film thickness of 1-20microns, such as 2-6 microns, is desired.

The compositions of the present invention can be used alone, or incombination with one or more other compositions, such as a coatingsystem having two or more layers. For example, the compositions of thepresent invention can comprise a colorant or not and can be used as aprimer, basecoat, and/or top coat. For substrates coated with multiplecoatings, one or more of those coatings can be coatings as describedherein. The present coatings can also be used as a packaging “size”coating, wash coat, spray coat, end coat, and the like.

It will be appreciated that the compositions described herein can beeither one component (“1K”), or multi-component compositions such as twocomponent (“2K”) or more. A 1K composition will be understood asreferring to a composition wherein all the coating components aremaintained in the same container after manufacture, during storage, etc.A 1K composition can be applied to a substrate and cured by anyconventional means, such as by heating, forced air, and the like. Thepresent compositions can also be multi-component, which will beunderstood as compositions in which various components are maintainedseparately until just prior to application. As noted above, the presentcompositions can be thermoplastic or thermosetting.

The composition can be a clearcoat. A clearcoat will be understood as acoating that is substantially transparent or translucent. A clearcoatcan therefore have some degree of color, provided it does not make theclearcoat opaque or otherwise affect, to any significant degree, theability to see the underlying substrate. The clearcoats of the presentinvention can be used, for example, in conjunction with a pigmentedbasecoat. The clearcoat can be formulated as is known in the coatingsart.

The composition may also comprise a colorant, such as a pigmentedbasecoat used in conjunction with a clearcoat, or as a pigmentedmonocoat. Such coating layers are used in various industries to impart adecorative and/or protective finish. For example, such a coating orcoating system may be applied to a vehicle. “Vehicle” is used herein inits broadest sense and includes all types of vehicles, such as but notlimited to cars, trucks, buses, vans, golf carts, motorcycles, bicycles,railroad cars, airplanes, helicopters, boats of any size and the like.It will be appreciated that the portion of the vehicle that is coatedaccording to the present invention may vary depending on why the coatingis being used. For example, anti-chip primers may be applied to some ofthe portions of the vehicle as described above. When used as a coloredbasecoat or monocoat, the present coatings will typically be applied tothose portions of the vehicle that are visible such as the roof, hood,doors, trunk lid and the like, but may also be applied to other areassuch as inside the trunk, inside the door and the like especially whenthe compositions are formulated as sealants or adhesives; they can alsobe applied to those portions of the car that are in contact with thedriver and/or passengers, such as the steering wheel, dashboard, gearshift, controls, door handle and the like. Clearcoats will typically beapplied to the exterior of a vehicle.

The compositions of the present invention are also suitable for use aspackaging coatings. The application of various pretreatments andcoatings to packaging is well established. Such treatments and/orcoatings, for example, can be used in the case of metal cans, whereinthe treatment and/or coating is used to retard or inhibit corrosion,provide a decorative coating, provide ease of handling during themanufacturing process, and the like. Coatings can be applied to theinterior of such cans to prevent the contents from contacting the metalof the container. Contact between the metal and a food, beverage orcosmetic, for example, can lead to corrosion of a metal container, whichcan then contaminate the food, beverage or cosmetic. This isparticularly true when the contents of the can are acidic in nature. Thecoatings applied to the interior of metal cans also help preventcorrosion in the headspace of the cans, which is the area between thefill line of the product and the can lid; corrosion in the headspace isparticularly problematic with food products having a high salt contentand/or that are high in acidity. Coatings can also be applied to theexterior of metal cans. Certain coatings of the present invention areparticularly applicable for use with coiled metal stock, such as thecoiled metal stock from which the ends of cans are made (“can endstock”), and end caps and closures are made (“cap/closure stock”). Sincecoatings designed for use on can end stock and cap/closure stock aretypically applied prior to the piece being cut and stamped out of thecoiled metal stock, they are typically flexible and extensible. Forexample, such stock is typically coated on both sides. Thereafter, thecoated metal stock is punched. For can ends, the metal is then scoredfor the “pop-top” opening and the pop-top ring is then attached with apin that is separately fabricated. The end is then attached to the canbody by an edge rolling process. A similar procedure is done for “easyopen” can ends. For easy open can ends, a score substantially around theperimeter of the lid allows for easy opening or removing of the lid fromthe can, typically by means of a pull tab. For caps and closures, thecap/closure stock is typically coated, such as by roll coating, and thecap or closure stamped out of the stock; it is possible, however, tocoat the cap/closure after formation. Coatings for cans subjected torelatively stringent temperature and/or pressure requirements shouldalso be resistant to popping, corrosion, blushing and/or blistering.

Accordingly, the present invention is further directed to a packagecoated at least in part with any of the coating compositions describedabove. A “package” is anything used to contain another item,particularly for shipping from a point of manufacture to a consumer, andfor subsequent storage by a consumer. A package will be thereforeunderstood as something that is sealed so as to keep its contents freefrom deterioration until opened by a consumer. The manufacturer willoften identify the length of time during which the food or beverage willbe free from spoilage, which typically ranges from several months toyears. Thus, the present “package” is distinguished from a storagecontainer or bakeware in which a consumer might make and/or store food;such a container would only maintain the freshness or integrity of thefood item for a relatively short period. A package according to thepresent invention can be made of metal or non-metal, for example,plastic or laminate, and be in any form. An example of a suitablepackage is a laminate tube. Another example of a suitable package ismetal can. The term “metal can” includes any type of metal can,container or any type of receptacle or portion thereof that is sealed bythe food/beverage manufacturer to minimize or eliminate spoilage of thecontents until such package is opened by the consumer. One example of ametal can is a food can; the term “food can(s)” is used herein to referto cans, containers or any type of receptacle or portion thereof used tohold any type of food and/or beverage. “Beverage can” may also be usedto refer more specifically to a food can in which a beverage ispackaged. The term “metal can(s)” specifically includes food cans(including beverage cans) and also specifically includes “can ends”including “E-Z open ends”, which are typically stamped from can endstock and used in conjunction with the packaging of food and beverages.The term “metal cans” also specifically includes metal caps and/orclosures such as bottle caps, screw top caps and lids of any size, lugcaps, and the like. The metal cans can be used to hold other items aswell, including, but not limited to, cosmetics, such as personal careproducts, bug spray, spray paint, and any other compound suitable forpackaging in an aerosol can. The cans can include “two piece cans” and“three-piece cans” as well as drawn and ironed cans; such cans oftenfind application with aerosol products. Packages coated according to thepresent invention can also include plastic bottles, plastic tubes,laminates and flexible packaging, such as those made from PE, PP, PETand the like. Such packaging could hold, for example, food, toothpaste,other personal care products and the like.

The present invention is also directed to a package coated with acoating comprising silicone at a wt % of 10 or greater, such as 15 wt %or greater or 20 wt % or greater, where wt % is based on the weight ofsolids, and wherein the package has a food release value of 90 percentor greater measured after four weeks in hot storage at 120° F. A methodfor measuring such food release is described in the examples.

The coating can be applied to the interior and/or the exterior of thepackage. For example, the coating can be rollcoated onto metal used tomake a two-piece food can, a three-piece food can, can end stock and/orcap/closure stock. The coating is applied to a coil or sheet by rollcoating; the coating is then cured and can ends are stamped out andfabricated into the finished product, i.e. can ends. The coating couldalso be applied as a rim coat to the bottom of the can; such applicationcan be by roll coating. The rim coat functions to reduce friction forimproved handling during the continued fabrication and/or processing ofthe can. The coating can also be applied to caps and/or closures; suchapplication can include, for example, a protective varnish that isapplied before and/or after formation of the cap/closure and/or apigmented enamel post applied to the cap, particularly those having ascored seam at the bottom of the cap. Decorated can stock can also bepartially coated externally with the coating described herein, and thedecorated, coated can stock used to form various metal cans.

Metal coils, having wide application in many industries, are alsosubstrates that can be coated according to the present invention. Coilcoatings also typically comprise a colorant.

After application to the substrate, the coating composition may be curedby any appropriate means. In some applications a cure of 425° F. orlower, such as 415 or lower or 400 or lower for 5 minutes or less, suchas 4.5 minutes or less may be desired and can be achieved according tothe present invention. Accordingly, the present coatings can be usedacross a broad range of industries and cure conditions.

As used herein, unless otherwise expressly specified, all numbers suchas those expressing values, ranges, amounts or percentages may be readas if prefaced by the word “about”, even if the term does not expresslyappear. Also, any numerical range recited herein is intended to includeall sub-ranges subsumed therein. Singular encompasses plural and viceversa. For example, although reference is made herein to “a” siliconeresin, “an” amine terminated polyamide, “an” EVO, “a” film formingcomponent, “a” film forming resin, “a” crosslinker and the like, one ormore of each of these and any other components can be used. As usedherein, the term “polymer” refers to oligomers and both homopolymers andcopolymers, and the prefix “poly” refers to two or more. (Meth)acrylic,and like terms, refers to both acrylic and methacrylic. Including, forexample and like terms means including, for example, but not limited to.When ranges are given, any endpoints of those ranges and/or numberswithin those ranges can be combined within the scope of the presentinvention. When maximum and minimum amounts are given, any such amountscan be combined to specify ranges of ingredients numbers within thoseranges can be combined within the scope of the present invention. Theword “comprising” and forms of the word “comprising”, as used in thisdescription and in the claims, does not limit the present invention toexclude any variants or additions. Additionally, although the presentinvention has been described in terms of “comprising”, the processes,materials, and coating compositions detailed herein may also bedescribed as “consisting essentially of” or “consisting of”.

Non-limiting aspects of the invention include:

1. A coating comprising:

-   -   a. epoxidized vegetable oil;    -   b. an amine terminated polyamide; and    -   c. a silicone resin; wherein the composition comprises 5 wt % or        greater epoxidized vegetable oil, where wt % is based on the        total solid weight of the composition.        2. The coating composition of Aspect 1, wherein the epoxidized        vegetable oil comprises epoxidized soy bean oil.        3. The coating composition of any of the preceding Aspects,        wherein the composition comprises 10 to 13 wt % epoxidized soy        bean oil, based on the total solid weight of the composition.        4. The coating of any of the preceding Aspects, wherein the        polyamide has an amine value of 220 to 250, as determined by        titration with HBr in HBr/Acetic acid using methyl violet        indictor.        5. The coating composition of any of the preceding Aspects,        wherein the silicone comprises a silanol functional        silsesquioxane silicone resin.        6. The coating composition of any of the preceding Aspects,        further comprising 30 wt % or less phenolic resin, where weight        percent is based on the total solid weight of the coating.        7. The coating composition of Aspect 6, wherein the composition        has 10 wt % or less phenolic resin, where wt % is based on the        total solids weight of the coating.        8. The coating composition of Aspect 6, wherein the composition        has 5 wt % or less phenolic resin, where wt % is based on the        total solid weight of the coating.        9. The coating composition of Aspect 6, wherein the composition        has 1 wt % or less phenolic resin, where wt % is based on the        total solid weight of the coating.        10. The coating composition of any of the preceding Aspects,        further comprising an acrylic resin.        11. The coating composition of Aspect 10, wherein the acrylic        resin comprises structural units derived from (meth)acrylic acid        and alkyl (meth)acrylate.        12. The coating composition of Aspect 10 or 11, wherein the        acrylic resin comprises a cyclic (meth)acrylate.        13. The coating composition of any of the preceding Aspects,        further comprising benzoguanamine.        14. The coating composition of any of the preceding Aspects,        wherein the composition and/or components thereof are        substantially free, essentially free, or completely free of BPA,        and derivatives thereof.        15. The coating composition of any of the preceding Aspects,        wherein the composition and/or components thereof are        substantially free, essentially free, or completely free of BPF,        and derivatives thereof.        16. The coating composition of any of the preceding Aspects,        wherein the composition and/or components thereof are        substantially free, essentially free, or completely free of        hydroxyl functional acrylic monomers.        17. The coating composition of any of the preceding Aspects,        wherein the composition and/or components thereof are        substantially free, essentially free, or completely free of        styrene.        18. The coating composition of any of the preceding Aspects,        wherein the composition and/or components thereof are        substantially free, essentially free, or completely free of        vinyl chloride monomers.        19. The coating composition of any of the preceding Aspects,        wherein the composition and/or components thereof are        substantially free, essentially free, or completely free of        ethyl acrylate.        20. The coating composition of any of the preceding Aspects,        wherein the composition and/or components thereof are        substantially free, essentially free, or completely free of        acrylamide, such as N-BMA.        21. A substrate coated at least in part with the coating        composition any of the preceding Aspects.        22. The substrate of Aspect 14, wherein the substrate comprises        a package.        23. The package of Aspect 15, wherein the package is a metal        can.        24. The package of Aspect 16, wherein the metal can is a food        can or beverage can.        25. The package of Aspect 16, wherein the food can or beverage        can is coated on the inside with the coating composition of any        Aspects 1-12.        26. The package of Aspect 17, wherein the efficiency of food        release from the metal can is greater than the efficiency of        food release from a metal can coated with a coating without        silicone.

EXAMPLES

The following examples are intended to illustrate the invention andshould not be construed as limiting the invention in any way.

Example 1

Coating composition A was made by mixing the ingredients shown below ina Cowels type mixer at high speed, 1100 rpm.

Coating A Resin Solids

cresol phenolic A¹ 26.4 Acrylic A 5 Epoxidized soya bean oil 10 Epikure3115³ 3.6 Acrylic B 20 Cymel 5010² 10 RSN 217 silicone⁴ 25 100 ¹cresolphenolic A = PR 516 from Allnex 62% solids ²Cymel 5010 = Benzoganimefrom Allnex ³Epikure 3115 = amine terminated polyamide ⁴RSN217 =Silsesquioxane silicone from Dow Chemical

Acrylic A Solids Styrene  25% Ethyl acrylate  53% Methacrylic acid  22%100% Acrylic B Solids Styrene  25% Ethyl Acrylate  42% Methacrylic acid 33% 100%

The mixture as prepared above was dispersed in water to 30% solids and aviscosity of 21 seconds as measured using a Ford cup #4 at a temperatureof 78° F.

Coating A Solution in Water

cresol phenolic A @ 62% solids in butanol 426 Acrylic A @ 52% solids inbutyl cellosolve 96 Epoxidized soya bean oil 100 Epikure 3115 @ 80%solids in butanol 45 Acrylic B @ 35% solids in water 571 Cymel 5010 @66% solids in butanol 152 RSN 217 silicone @ 70% solids in butanol 357D.I. Water 176 1410 Total 3333

Example 2

Coating composition B was made as described for Example 1 by mixing theingredients shown below.

Coating B Resin Solids

cresol phenolic A 25 Acrylic A 5 Epoxidized soya bean oil 7.5 Epikure3115 7.5 Acrylic B 17.5 Cymel 5010 7.5 RSN 217 silicone 30 100

Coating B Solution in Water

cresol phenolic A @ 62% solids in butanol 403 Acrylic A @ 52% solids inbutyl cellosolve 96 Epoxidized soya bean oil 75 Epikure 3115 @ 80%solids in butanol 94 Acrylic B @ 35% solids in water 500 Cymel 5010 @66% solids in butanol 121 RSN 217 silicone @ 70% solids in butanol 429D.I. Water 1615.0 Total 3333

Example 3

Coating composition C was made as described in Example 1 by mixing theingredients shown below.

Coating C Resin Solids

cresol phenolic B⁵ 25 Acrylic A 3 Epoxidized soya bean oil 15 Epikure3115 5 Acrylic B 27 Cymel 5010 10 RSN 217 silicone 15 100 ⁵Creso1phenolic B = PR520 from Allnex 62% solids

Coating C Solution in Water

cresol phenolic B @ 62% solids in butanol 403 Acrylic A @ 52% solids inbutanol 58 Epoxidized soya bean oil 150 Epikure 3115 @ 80% solids inbutanol 50 Acrylic B @ 35% solids in water 771 Cymel 5010 @ 66% solidsin butanol 152 RSN 217 silicone @ 70% solids in butanol 214 D.I. Water1535.0 Total 3333

Example 4

Coating composition D was made as described in Example 1 by mixing theingredients shown below.

Coating D Resin Solids Acrylic B 18.5 Epoxidized soya oil 12.3Epikure3115 7.6 RSN233 silicone⁵ 49 Cymel 5010 12.6 100 ⁵RSN233Silsesquioxane silicone from Dow

Coating D Solution in Water

Acrylic B solution in water @ 35% solids in butanol. 529 Epoxidized soyaoil 123 Epikure 3115 @ 80% solids in butanol 95 RSN233 silicone @ 70%solids in butanol 700 Cymel 5010 @ 66% solids in butanol 191 D.I. water1696 Total 3333

Example 5

Coating composition E was made as described in Example 1 by mixing theingredients shown below.

Coating E Resin Solids

Cresol phenolic B 25 Acrylic B 20 Epoxidized Soya Oil 5 EpiKure 3115 7.5Cyme15010 22.5 RSN233 silicone 20 Total 100

Coating E Solution in Water Acrylic B solution in water @ 35% solids inbutanol 571 Cresol phenolic B at 62% solids in butanol 403 Epoxidizedsoya oil 50 Epikure 3115 @ 80% solids in butanol 94 RSN233 silicone @70% solids in butanol 286 Cymel 5010 @ 66% solids in butanol 341 D.I.water 1588 Total 3333

Example 6

Coating composition F was made by mixing the ingredients shown below.

Coating F Resin Solids

cresol phenolic A 30 Acrylic C 5 Epoxidized soya bean oil 10 Epikure3115 10 Acrylic D 17 Cymel 1123⁶ 12 RSN 217 silicone 16 100 ⁶Cyme1 1123= Benzoganime from Allnex

Acrylic A Solids Methyl Methacrylate  25% Ethyl acrylate  53%Methacrylic acid  22% 100% Acrylic B Solids Methyl Methacrylate  25%Ethyl Acrylate  42% Methacrylic acid  33% 100%

Example 7

Coatings A-F were airless spray applied onto 300×407 can to a filmweight of 280-300 MGS with a Sprimag commercial spray machine usingNordson MEG guns with the following dwell times and spray nozzles.

Spray Parameters

Dwell Time in Millisecounds Nozzle Type Pressure Gun #1 108 MS 1097007750 psi Gun #2 100 Ms 121999 800 psi

Commercially available 2 piece water-based interior spray for food canshaving the composition shown below were also sprayed in the same manner.

Resin Solids

Cresol phenolic A 50 Acrylic A 10 Epikure 3115 10 Acrylic B 20 Cymel5010 10 100

Commercial Coating in Water

Cresol phenolic A @ 62% solids in butanol 806 Acrylic A 52% solids inbutanol 192 Epikure 3115 @ 80% solids in butanol 125 Acrylic B @ 35% %solids in water 571 Cymel 5010 @ 66% % solids in butanol 152 D.I. water1486 Total 3333The commercial coatings is 30% solids in water at a viscosity of 21 secas measured by a #4 Ford cup at a temperature of 78° F.

The sprayed cans were cured in an inside bake oven at 425° F. for 5minutes and put into test pack. For the test pack, commerciallyavailable Chicken Noodle Soup was heated to 160° F. then put into thesprayed and cured 300×407 cans with a 3/16 in headspace. An end wasseamed on the cans. The cans were then steam processed at 250° F. forone hour. After processing, the cans were then cooled to roomtemperature overnight and finally stored at 120° F. for one or twoweeks. Following either one or two weeks, as indicated below, corrosionwas rated visually on a scale of 1-10 with 10 being no corrosion. Arating of 8.5 or higher is considered commercially acceptable.

The top of a DWI can is more prone to corrosion because of the reducedlevel of tin compared to the bottom of the can due to the drawingprocess.

The results obtained are shown below.

Test Pack Results - Coating A - Coating C versus Commercial CoatingCorrosion top ¼ in of 300 × 407 Corrosion top 1 Corrosion top ¼ inCorrosion top 1 Corrosion top ¼ in Corrosion top 1 inch can inch of canof 300 × 407 can inch of can of 300 × 407 can of can Coating A Coating BCoating C 1 Week at 120° F. 1 Week at 120° F. 1 Week at 120° F. 1 Weekat 120° F. 1 Week at 120° F. 1 Week at 120° F. Can1 10 10 8.5 8.7 10 9Can2 9.2 9.8 8.9 9.7 9.7 9 Can3 9.7 9.3 9 9.5 9.7 9.8 2 Weeks at 2 Weeksat 120° F. 120° F. 2 Weeks at 120° F. 2 Weeks at 120° F. 2 Weeks at 120°F. 2 Weeks at 120° F. Can1 9.5 9.9 9.5 9.9 8.5 9.00 Can2 9.7 9.9 8.6 8.69.5 9.7 Can3 9.7 9.9 8.5 9.4 9.7 9.8 Commercial Coating CommercialCoating Commercial Coating 1 Week at 120° F. 1 Week at 120° F. 1 Week at120° F. 1 Week at 120° F. 1 Week at 120° F. 1 Week at 120° F. Can1 10 109.2 9.5 10 10 Can2 10 10 10 9.9 10 10 Can3 9.8 9.9 10 10 10 9.8 2 Weeksat 2 Weeks at 120° F. 120° F. 2 Weeks at 120° F. 2 Weeks at 120° F. 2Weeks at 120° F. 2 Weeks at 120° F. Can1 9.5 9.7 10 10 10 9.8 Can2 8.99.9 9.8 9.9 9.7 9.7 Can3 10.0 10 9.9 10 8.9 9.2 Test Pack Results -Coating D and E versus Commercial Coating Corrosion top ¼ in ofCorrosion top 1 inch of Corrosion top ¼ in of Corrosion top 1 inch 300 ×407 can can 300 × 407 can of can Coating D Coating E 1 Week at 120° F. 1Week at 120° F. 1 Week at 120° F. 1 Week at 120° F. Can 1 9.8 9.6 8.38.1 Can 2 9.8 9.6 8.2 8 Can 3 9.7 9.5 8.3 8.1 2 Weeks at 120° F. 2 Weeksat 120° F. 2 Weeks at 120° F. 2 Weeks at 120° F. Can 1 9.6 9.4 8.1 7.9Can 2 9.7 9.5 7.9 7.7 Can 3 9.5 9.3 7.8 7.7 Commercial CoatingCommercial Coating 1 Week at 120° F. 1 Week at 120° F. 1 Week at 120° F.1 Week at 120° F. Can 1 9.4 9.3 9.8 9.7 Can 2 10 9.9 10 10 Can 3 10 1010 9.8 2 Weeks at 120° F. 2 Weeks at 120° F. 2 Weeks at 120° F. 2 Weeksat 120° F. Can 1 10 10 10 9.8 Can 2 9.8 9.9 9.7 9.7 Can 3 9.9 10 8.9 9.2Test Pack Results - Coating F Corrosion top ¼ in of Corrosion top 1 inchof 300 × 407 can can 1 Week at 120° F. 1 Week at 120° F. Can 1 9.2 9.5Can 2 8.1 9.2 Can 3 7.6 9.0 2 Weeks at 120° F. 2 Weeks at 120° F. Can 16.8 8.6 Can 2 7.8 9.0 Can 3 7.6 8.9

As can be seen, the compositions of the present invention achievedcommercially acceptable or near acceptable corrosion resistance withless phenolic than the commercial product; coating D, having no addedphenolic, also performed to acceptable commercial standards.

Example 7

Coating E was airless spray applied onto 300×407 can to a film weight of280-300 MGS with a Sprimag commercial spray machine using Nordson MEGguns with the dwell times and spray nozzles indicated in Example 6. Thecans were tested for soup release using the following test:

Soup Release Test for thick condensed soup (green pea soup)

Tested in triplicate for each coating tested.

Repack Procedure

-   -   Heated soup to 130° F.    -   Put soup into test cans, leaving ¼ inch headspace    -   Steam processed 30 minutes at 250° F., end up    -   Cans allowed to air cool, end up, overnight, before testing for        soup release    -   Cans were then placed in Hot Room, end up, for time indicated        below.        After required time of storage, test cans were cooled before        testing for soup release.

Soup Release Procedure

-   -   Tare balance with an empty can that has been side cut    -   Weighed test can of soup    -   Shake control can downward @ a 90° angle until soup falls out.    -   Test cans were given the same amount of consecutive shakes or        until soup falls out of can, weight and number of shakes        recorded

Soup Release Calculations

-   -   Start weight (end removed) A    -   Weight of can after shaking B    -   Amount of soup released C        (A−B=C)    -   Calculated percentage of soup released

Commercially obtained Condensed Green Pea Soup, packaged in cans coatedwith a commercially available gold epoxy that does not contain siliconewere also tested after hot room exposure. The table below reports theaverage percent of soup released and number of shakes.

Coating E Commercial Epoxy Gold 2 weeks storage at 120° F. Averagepercent food release 98.6 0.01 Average number of shakes to release food7.7 15 4 weeks storage at 120° F. Average percent food release 98.9 0.1Average number of shakes to release food 5.0 66.7

As can be seen in the table, the ease of removing the food from a can,and the amount removed, is greatly increased using the siliconecontaining coating of the present invention, as compared with acommercially available product.

Whereas particular embodiments of this invention have been describedabove for purposes of illustration, it will be evident to those skilledin the art that numerous variations of the details of the presentinvention may be made without departing from the invention as defined inthe appended claims.

What is claimed is:
 1. A coating composition comprising: a. epoxidizedvegetable oil; b. an amine terminated polyamide; and c. a silicone resincomprising a fully phenylated silsesquioxane wherein the phenyl groupsof the phenylated silsesquioxane are unsubstituted; wherein the coatingcomposition comprises 5 wt % or greater epoxidized vegetable oil, wherewt % is based on the total solid weight of the coating composition. 2.The coating composition of claim 1, further comprising 30 wt % or lessphenolic resin, where weight percent is based on the total solid weightof the coating composition.
 3. The coating composition of claim 1,wherein the epoxidized vegetable oil comprises epoxidized soy bean oil.4. The coating composition of claim 1, wherein the epoxidized vegetableoil comprises 10 to 13 wt % epoxidized soy bean oil, where wt % is basedon the total solid weight of the coating composition.
 5. The coatingcomposition of claim 1, further comprising an acrylic resin.
 6. Thecoating composition of claim 5, wherein the acrylic resin is formed frommonomers comprising (meth)acrylic acid and alkyl acrylate.
 7. Thecoating composition of claim 1, wherein the polyamide has an amine valueof 220 to 250, as determined by titration with HBr in HBr/Acetic acidusing methyl violet indictor.
 8. The coating composition of claim 1,wherein the silicone resin comprises a silanol functional silsesquioxanesilicone resin and the coating composition has 10 wt % or less phenolicresin, where wt % is based on the total solid weight of the coatingcomposition.
 9. The coating composition of claim 8, wherein thecomposition has 5 wt % or less phenolic resin, where wt % is based onthe total solid weight of the coating composition.
 10. The coatingcomposition of claim 8, wherein the composition has 1 wt % or lessphenolic resin, where wt % is based on the total solid weight of thecoating composition.
 11. The coating of claim 1, wherein the coatingfurther comprises benzoguanamine.
 12. A substrate coated at least inpart with the coating composition of claim
 1. 13. A substrate coated atleast in part with the coating composition of claim
 8. 14. The substrateof claim 12, wherein the substrate comprises a package.
 15. Thesubstrate of claim 13, wherein the substrate comprises a package. 16.The package of claim 14, wherein the package is a metal can.
 17. Thepackage of claim 15, wherein the package is a metal can.
 18. The packageof claim 16, wherein the efficiency of food release from the metal canis greater than the efficiency of food release from a metal can coatedwith a coating without silicone.
 19. The package of claim 17 wherein theefficiency of food release from the metal can is greater than theefficiency of food release from a metal can coated with a coatingwithout silicone.
 20. The coating composition of claim 1, wherein thecomposition does not include styrene.
 21. The coating composition ofclaim 1, wherein the composition does not include ethyl acrylate. 22.The coating composition of claim 1, wherein the composition does notinclude n-butoxy methyl acrylamide.
 23. The coating composition of claim5, wherein the acrylic resin is formed from monomers comprising cyclic(meth)acrylate.